Modular Access to Diverse Chemiluminescent Dioxetane-Luminophores through Convergent Synthesis

Area of Science:

• Organic Chemistry
• Chemical Biology
• Materials Science

Background:

• Adamantyl-dioxetane luminophores are crucial chemiluminescent probes for biological diagnostics and imaging.
• Existing synthetic routes can be complex and limit the exploration of novel structures.

Purpose of the Study:

• To develop a new, efficient synthetic route for adamantyl-dioxetane chemiluminescent luminophores.
• To enable rapid exploration and synthesis of novel luminogenic molecular structures.

Main Methods:

• Utilized a convergent synthesis employing an unusual Stille cross-coupling reaction with a stannane-enolether.
• Directly synthesized adamantyl-enolether precursors.
• Obtained dioxetanes via singlet-oxygen oxidation of the enolether precursor.

Main Results:

• Developed an efficient and broad-scope synthetic route for adamantyl-enolether precursors.
• Demonstrated a simple, one-step oxidation to yield dioxetane luminophores.
• The strategy allows for late-stage derivatization, facilitating library synthesis.

Conclusions:

• The new synthetic strategy offers a streamlined approach to known and novel adamantyl-dioxetane luminophores.
• This method is expected to accelerate the discovery and development of new chemiluminescent probes for diagnostics and imaging.